The first issue was published on February 16, 1990, and featured singer k.d. lang on its cover. The cover price was $1.95 (equivalent to $3.65 in 2017) The title word entertainment was not capitalized on the cover until mid-1992 and has remained so since. By 2003, the magazine's weekly circulation averaged 1.7 million copies per week. In March 2006, managing editor Rick Tetzeli oversaw an overhaul of EW's graphics and layout to reflect a more-modern look.

Created by Jeff Jarvis and founded by Michael Klingensmith, who served as publisher until October 1996, the magazine's original television advertising soliciting pre-publication subscribers portrayed it as a consumer guide to popular culture, including movies, music, and book reviews, sometimes with video game and stage reviews, too. ("the post-modern Farmers' Almanac").

In September 2016, in collaboration with People, Entertainment Weekly launched the People/Entertainment Weekly Network. The network is "a free, ad-supported online-video network carries short- and long-form programming covering celebrities, pop culture, lifestyle and human-interest stories". It was rebranded as PeopleTV in September 2017.